EP2354238A1 - Procédés pour la préparation de sels de phosphatides - Google Patents
Procédés pour la préparation de sels de phosphatides Download PDFInfo
- Publication number
- EP2354238A1 EP2354238A1 EP10154488A EP10154488A EP2354238A1 EP 2354238 A1 EP2354238 A1 EP 2354238A1 EP 10154488 A EP10154488 A EP 10154488A EP 10154488 A EP10154488 A EP 10154488A EP 2354238 A1 EP2354238 A1 EP 2354238A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- salt
- lecithin
- complex
- mixture
- pld
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 37
- 230000008569 process Effects 0.000 title claims abstract description 37
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 150000003839 salts Chemical class 0.000 title claims abstract description 7
- 239000000203 mixture Substances 0.000 claims abstract description 29
- 238000006243 chemical reaction Methods 0.000 claims abstract description 28
- 239000000243 solution Substances 0.000 claims abstract description 28
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims abstract description 27
- 102000011420 Phospholipase D Human genes 0.000 claims abstract description 27
- 108090000553 Phospholipase D Proteins 0.000 claims abstract description 27
- 229940067606 lecithin Drugs 0.000 claims abstract description 27
- 239000000787 lecithin Substances 0.000 claims abstract description 27
- 235000010445 lecithin Nutrition 0.000 claims abstract description 27
- 239000002994 raw material Substances 0.000 claims abstract description 14
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000000758 substrate Substances 0.000 claims abstract description 5
- 239000007864 aqueous solution Substances 0.000 claims abstract description 4
- 150000001412 amines Chemical class 0.000 claims abstract description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 3
- 150000004665 fatty acids Chemical group 0.000 claims abstract description 3
- 150000003904 phospholipids Chemical class 0.000 claims description 14
- JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 claims description 6
- 229940083466 soybean lecithin Drugs 0.000 claims description 6
- JQWAHKMIYCERGA-UHFFFAOYSA-N (2-nonanoyloxy-3-octadeca-9,12-dienoyloxypropoxy)-[2-(trimethylazaniumyl)ethyl]phosphinate Chemical compound CCCCCCCCC(=O)OC(COP([O-])(=O)CC[N+](C)(C)C)COC(=O)CCCCCCCC=CCC=CCCCCC JQWAHKMIYCERGA-UHFFFAOYSA-N 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 241000251468 Actinopterygii Species 0.000 claims description 2
- 240000002791 Brassica napus Species 0.000 claims description 2
- 235000004977 Brassica sinapistrum Nutrition 0.000 claims description 2
- 235000013336 milk Nutrition 0.000 claims description 2
- 239000008267 milk Substances 0.000 claims description 2
- 210000004080 milk Anatomy 0.000 claims description 2
- 229940005741 sunflower lecithin Drugs 0.000 claims description 2
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 8
- 229960001153 serine Drugs 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- TZCPCKNHXULUIY-RGULYWFUSA-N 1,2-distearoyl-sn-glycero-3-phosphoserine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCCCC TZCPCKNHXULUIY-RGULYWFUSA-N 0.000 description 5
- ZWZWYGMENQVNFU-UHFFFAOYSA-N Glycerophosphorylserin Natural products OC(=O)C(N)COP(O)(=O)OCC(O)CO ZWZWYGMENQVNFU-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 4
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 4
- 239000001110 calcium chloride Substances 0.000 description 4
- 229910001628 calcium chloride Inorganic materials 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229960002446 octanoic acid Drugs 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 229940024606 amino acid Drugs 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- PORPENFLTBBHSG-MGBGTMOVSA-N 1,2-dihexadecanoyl-sn-glycerol-3-phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC PORPENFLTBBHSG-MGBGTMOVSA-N 0.000 description 2
- 240000007124 Brassica oleracea Species 0.000 description 2
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 2
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 2
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000187180 Streptomyces sp. Species 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 235000013376 functional food Nutrition 0.000 description 2
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 150000008106 phosphatidylserines Chemical class 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 206010012289 Dementia Diseases 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 208000010877 cognitive disease Diseases 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000004925 denaturation Methods 0.000 description 1
- 230000036425 denaturation Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002996 emotional effect Effects 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 229960000890 hydrocortisone Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000036651 mood Effects 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000008103 phosphatidic acids Chemical class 0.000 description 1
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000000697 serotonin reuptake Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
- C12P7/6445—Glycerides
- C12P7/6481—Phosphoglycerides
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/04—Alpha- or beta- amino acids
- C12P13/06—Alanine; Leucine; Isoleucine; Serine; Homoserine
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P9/00—Preparation of organic compounds containing a metal or atom other than H, N, C, O, S or halogen
Definitions
- the present invention relates to processes for the preparation of phosphatide-salt complexes.
- the present invention relates to processes for the preparation of phosphatidylserine-salt complexes and phosphatidic-acid-salt complexes using carboxylate-salt complexes that are reacted in aqueous systems.
- Phosphatidylserine salts and phosphatidic-acid salts are used in pharmaceutical compositions, nutritional compounds, and functional foods.
- the importance of phosphatidylserine as a functional ingredient is supported by the US FDA's qualified health claims in which the usage of phosphatidylserine was related to the reduction of cognitive dysfunction and dementia in the elderly.
- Rutenberg in US Patent No. 6,410,522 (assigned to the assignee of the present invention and hereby incorporated by reference as if fully set forth herein), teaches an anti-depressant, stress suppressor, and mood improver having a prominent action for decreasing blood cortisol level and serotonin reuptake, and has an effect of alleviating symptoms associated with depression and mental & emotional stress of a subject administered with the improver.
- De Ferra et al. in US Patent No. 6,492,146 (hereinafter De Ferra '146), disclose a process for the preparation of phosphatidylserine (PS) with racemic or enantiomerically pure serine in the presence of the enzyme phospholipase-D (PLD) and a surfactant in a quantity not greater than 0.4 grams per gram of substrate in which the reaction medium is an aqueous dispersion free of organic solvents.
- PS phosphatidylserine
- PLD phospholipase-D
- surfactant in a quantity not greater than 0.4 grams per gram of substrate in which the reaction medium is an aqueous dispersion free of organic solvents.
- the main advantage of the process is the possibility to carry out the transphosphatidylation reaction of phosphatidylcholine, and of similar phosphatides in an aqueous medium, to obtain phosphatidylserine of good purity with highly-satisfactory yields and with minimal phosphatidic acid (PA) by-product.
- PA phosphatidic acid
- Schmitt et al. in Patent DE 19917249 (hereinafter Schmitt '249), disclose a process for the preparation of PS salt by adding L-serine to an aqueous dispersion of lecithin (1-20% w/w), adding a PLD and CaCl 2 solution to the dispersion, stirring the mixture at room temperature for 10-20 hours, separating the resulting PS-Ca salt from the aqueous phase, washing the Ca salt with water to remove L-serine and extracting the product with ethanol.
- a solvent is used to completely dissolve the lecithin in transphosphatidylation reactions.
- a dissolved solution as opposed to a suspension, makes the process easier to manage.
- surfactant is used to enable a manageable solution/dispersion of the lecithin substrate.
- Embodiments of the present invention provide a process in which PA-salt complexes and/or PS-salt complexes are produced from lecithin by enzymatic conversion in an aqueous solution of racemic or enantiomerically-pure serine, preferably with (L)-serine utilizing PLD and an aqueous carboxylate-salt complex solution (C2-C8) in the absence of surfactants.
- Embodiments of the present invention further provide a process for the simultaneous preparation of stable PA-salt complexes and PS-salt (PS-salt) complexes in low-cost industrial scale as an ingredient for dietetic and functional food applications, as well as a process which is safe and does not necessitate further costly extraction of surfactants from the reaction mixture.
- PS-salt PS-salt
- a process for the preparation of phosphatide-salt complexes including the steps of: (a) using at least one raw material lecithin as a substrate; and (b) enzymatically processing at least one raw material lecithin with phospholipase-D (PLD), racemic or enantiomerically-pure serine, and/or amine in an aqueous carboxylate-salt-complex solution, wherein the step of processing is performed in a single-phase reaction environment, to produce phosphatide-salt complexes having a structural fatty-acid chain derived from at least one raw material lecithin.
- PLD phospholipase-D
- At least one raw material lecithin is selected from the group consisting of: a vegetal lecithin and a non-vegetal lecithin;
- the vegetal lecithin is selected from the group consisting of: soybean lecithin, sunflower lecithin, and rapeseed lecithin;
- the non-vegetal lecithin is selected from the group consisting of: milk phospholipids, egg yolk lecithin, and fish lecithin;
- the PLD is selected from the group consisting of: vegetal PLD, bacterial-originated enzyme PLD, a combination of vegetal PLD and bacterial-originated enzyme PLD.
- the step of processing is performed at a pH in the range of about 4.5-8.0 at a temperature in the range of about 25-60°C.
- the aqueous carboxylate-salt-complex solution is formed from an aqueous solution of a carboxylic acid with a chain length of C2-C8 and a salt in an approximately 1:2 (weight per weight) acid-to-salt ratio.
- the process further includes the step of: (c) denaturing the PLD upon treatment with at least one component selected from the group consisting of: a suitable organic solvent and heat.
- the phosphatide-salt complexes include a mixture of phosphatidic-acid-salt (PA-salt) complex and phosphatidylserine-salt (PS-salt) complex.
- PA-salt phosphatidic-acid-salt
- PS-salt phosphatidylserine-salt
- the mixture has a product yield of at least 3% (w/w) PA-salt complex and at least 20% (w/w) PS-salt complex out of the total phospholipid content of the mixture.
- the mixture has a product yield above about 10% (w/w) PA-salt complex and at least 20% (w/w) PS-salt complex out of the total phospholipid content of the mixture.
- the mixture has a product yield of 20-70% (w/w) PA-salt complex and at least 20% (w/w) PS-salt complex out of the total phospholipid content of the mixture.
- the present invention relates to processes for the preparation of phosphatide-salt complexes.
- the principles and operation for preparing phosphatide-salt complexes, according to the present invention may be better understood with reference to the accompanying description.
- Exemplary embodiments of the present invention are detailed below in the following three examples of the synthetic processes.
- PS-salt complex was produced by the following process:
- caprylate-calcium-salt-complex solution which corresponds to the general carboxylate-salt-complex solution.
- the phospholipids complex layer was removed and then dried under reduced pressure at a constant temperature of 30°C.
- the final composition of PA-salt complex and PS-salt complex as measured by HPTLC was: PS-salt complex 27.3%, PA-salt complex 6.6%.
- PS-salt complex Using egg yolk lecithin as the raw material, PS-salt complex and PA-salt complex were produced simultaneously by the following process:
- caprylate-calcium-salt-complex solution which corresponds to the general carboxylate-salt-complex solution.
- PS-salt complex 22.1%
- PA-salt complex 24.3%
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/700,073 US8546104B2 (en) | 2008-08-07 | 2010-02-04 | Processes for the preparation of phosphatide salts |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP2354238A1 true EP2354238A1 (fr) | 2011-08-10 |
| EP2354238B1 EP2354238B1 (fr) | 2019-03-20 |
Family
ID=43356310
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP10154488.0A Active EP2354238B1 (fr) | 2010-02-04 | 2010-02-24 | Procédés pour la préparation de sels de phosphatides |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US8546104B2 (fr) |
| EP (1) | EP2354238B1 (fr) |
| JP (1) | JP2011160795A (fr) |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19917249A1 (de) | 1999-02-26 | 2000-09-07 | Meyer Lucas Gmbh & Co | Verfahren zur Herstellung von Phosphatidylserin (PS) undd PS in Weichgelatinekapseln |
| US6410522B1 (en) | 2000-10-23 | 2002-06-25 | Lipogen Ltd. | Anti-depressant, stress suppressor and mood improver |
| EP1223222A1 (fr) * | 2001-01-11 | 2002-07-17 | Rinoru Oil Mills Co., Ltd. | Procédé pour le remplacement de bases dans les phospholipides |
| EP1231213A1 (fr) * | 2001-02-09 | 2002-08-14 | FIDIA FARMACEUTICI S.p.A. | Procédé de préparation des phosphatides et leur utilisation dans les domaines cosmétique, pharmaceutique et alimentaire |
| US6492146B1 (en) | 1999-04-28 | 2002-12-10 | Chemi S.P.A. | Process for the preparation of phosphatidylserines |
| EP2151499A2 (fr) * | 2008-08-07 | 2010-02-10 | Lipogen Ltd. | Procédés pour la préparation de phosphatides |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2348390C (fr) | 1998-10-30 | 2008-11-25 | Merck Patent Gesellschaft Mit Beschraenkter Haftung | Composition de traitement et de prevention de troubles neurologiques et psychopathologiques |
| ATE287448T1 (de) * | 1999-06-15 | 2005-02-15 | Yissum Res Dev Co | Enzymatische herstellung von phospholipiden in wässrigen medien |
| IL150240A (en) * | 2002-06-16 | 2005-07-25 | Lipogen Ltd | Infant formula supplemented with phospholipids |
| WO2005090587A1 (fr) | 2004-03-18 | 2005-09-29 | Nagase Chemtex Corporation | Procede d’enlevement d’enzyme et procede d’echange de base ou hydrolyse de phospholipide utilisant ledit procede |
-
2010
- 2010-02-04 US US12/700,073 patent/US8546104B2/en active Active
- 2010-02-24 EP EP10154488.0A patent/EP2354238B1/fr active Active
- 2010-08-02 JP JP2010173300A patent/JP2011160795A/ja active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19917249A1 (de) | 1999-02-26 | 2000-09-07 | Meyer Lucas Gmbh & Co | Verfahren zur Herstellung von Phosphatidylserin (PS) undd PS in Weichgelatinekapseln |
| US6492146B1 (en) | 1999-04-28 | 2002-12-10 | Chemi S.P.A. | Process for the preparation of phosphatidylserines |
| US6410522B1 (en) | 2000-10-23 | 2002-06-25 | Lipogen Ltd. | Anti-depressant, stress suppressor and mood improver |
| EP1223222A1 (fr) * | 2001-01-11 | 2002-07-17 | Rinoru Oil Mills Co., Ltd. | Procédé pour le remplacement de bases dans les phospholipides |
| EP1231213A1 (fr) * | 2001-02-09 | 2002-08-14 | FIDIA FARMACEUTICI S.p.A. | Procédé de préparation des phosphatides et leur utilisation dans les domaines cosmétique, pharmaceutique et alimentaire |
| EP2151499A2 (fr) * | 2008-08-07 | 2010-02-10 | Lipogen Ltd. | Procédés pour la préparation de phosphatides |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2354238B1 (fr) | 2019-03-20 |
| US20110212922A1 (en) | 2011-09-01 |
| JP2011160795A (ja) | 2011-08-25 |
| US8546104B2 (en) | 2013-10-01 |
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